Water → 3-(1-Adamantyl)-1-bromo-4-methoxyethoxymethoxybenzene

HRID 1957692Notes

Reaction equation

HRID 1957692 reaction equation
[H-].[Na+].[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[OH:20])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26]Cl.O>CN(C=O)C>[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[O:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[CH2:4][CH:5]3[CH2:11][CH:9]([CH2:8][CH:7]([CH2:6]3)[CH2:12]1)[CH2:10]2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 46704942-(1-Adamantyl)-4-bromophenol

Product 1

HCID 153780873-(1-Adamantyl)-1-bromo-4-methoxyethoxymethoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

3.8 g (0.13 mol) of sodium hydride (80% in oil) and 50 ml of DMF were introduced into a three-necked flask under a stream of nitrogen and a solution of 40 g (0.13 mol) of 2-(1-adamantyl)-4-bromophenol in 100 ml of DMF was added dropwise. The mixture was stirred until the evolution of gas had ceased. A solution of 18 ml (0.15 mol) of 2-methoxyethoxymethyl chloride in 20 ml of DMF was then added dropwise and the mixture was stirred for four hours at room temperature. The reaction medium was poured into water and extracted with ethyl ether. The organic phase was separated out after settling had taken place, washed with water, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a column of silica, eluted with a mixture of dichloromethane and hexane (50/50). After evaporation of the solvents, 40.1 g (78%) of the expected compound, having a melting point of 69°-70° C., were recovered.

Workup

  1. stirringthe mixture was stirred for four hours at room temperature
  2. extractionextracted with ethyl ether
  3. customThe organic phase was separated out
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by chromatography on a column of silica
  8. washeluted with a mixture of dichloromethane and hexane (50/50)
  9. customAfter evaporation of the solvents, 40.1 g (78%) of the expected compound
  10. customwere recovered

Sources & evidence

ORD record
ord-7c22755759334bd19723823fc15a8fe4
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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